Water → tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

HRID 1741593

반응식

HRID 1741593 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]=[N+]=[N-])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 23282934N-Boc-4-(2-azidoethyl)piperidine

생성물 1

HCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-(N-Boc-4-piperidinyl)ethylazide (19.3 g, 0.076 moles) in THF (400 ml)/H2O (195 ml) was added triphenylphosphine (80.0 g, 0.305 moles) in one portion at room temperature. This was stirred at room temperature 3 hours and the organic solvents were then removed in vacuo. The residue was acidified to pH 2 with 10% KHSO4 solution and this was extracted 4×100 ml portions of EtOAc. The organic extract was extracted with 2×100 ml portions of 10% KHSO4 and the aqueous phases were combined and the pH was adjusted to 10 with 2N NaOH. This solution was extracted with 4×200 ml portions of CH2Cl2. These were combined, dried (MgSO4) and the solvent was removed to give 1-2 as an oil. Rf 0.3 (silica gel, eluting with 10% CH3OH in CHCl3 /NH3).

후처리

  1. customthe organic solvents were then removed in vacuo
  2. extractionthis was extracted 4×100 ml portions of EtOAc
  3. extractionThe organic extract
  4. extractionwas extracted with 2×100 ml portions of 10% KHSO4
  5. extractionThis solution was extracted with 4×200 ml portions of CH2Cl2
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed

출처 및 근거

ORD 기록
ord-71c0794112134c4d8b45ac9d8e251579
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334596

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